Sodium Cyanide → (2-Cyanophenyl)acetic acid

HRID 1196572Notes

Reaction equation

HRID 1196572 reaction equation
[N+]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][C:11]([OH:13])=[O:12])([O-])=O.[C-:14]#[N:15].[Na+]>[Pd].[OH-].[Na+]>[C:14]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][C:11]([OH:13])=[O:12])#[N:15]

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 77337(2-Nitrophenyl)acetic acid

Product 1

HCID 87755(2-Cyanophenyl)acetic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 14798Sodium HydroxideSolvent

Procedure

2-Nitrophenylacetic acid (ex Aldrich) (18.1 g) dissolved in 0.1M.aq.sodium hydroxide (100 ml) was subjected to catalytic hydrogenation (at 30-40 psi) over 10% palladium on charcoal (2 g) until uptake ceased. The resultant solution was subjected first to diazotisation and then reaction with sodium cyanide and cuprous cyanide according to Simchen and Hafner, Ann. Chem., 1974, 1802 to give crude 2-cyanophenylacetic acid (14.9 g). The latter was treated with phosphorous pentachloride (20.6 g) and anhydrous hydrogen chloride in di-n-butyl ether (250 ml) for 2 hours. After a further 18 hours the volatiles were removed, the residue washed with water and recrystallized from ethanol to give 1-chloro-3-hydroxy-isoquinoline (1.48 g).

Sources & evidence

ORD record
ord-9c46674a505443329b8f608854c3f72f
Source dataset
uspto-grants-1992_05
Patent number
US05114940

Reaction notes

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